1-Methylpiperidin-3-amine dihydrochloride → (+/-) 9-fluoro-10-(3-hydroxy-3-methyl-but-1-ynyl)-N3-(1-methyl-3-piperidyl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-2,3-dicarboxamide

HRID 575166Notes

Reaction equation

HRID 575166 reaction equation
[C:1]([C:4]1[N:5]=[C:6]2[C:12]3[CH:13]=[C:14]([C:18]#[C:19][C:20]([OH:23])([CH3:22])[CH3:21])[C:15]([F:17])=[CH:16][C:11]=3[O:10][CH2:9][CH2:8][N:7]2[C:24]=1[C:25]([OH:27])=O)(=[O:3])[NH2:2].Cl.Cl.[CH3:30][N:31]1[CH2:36][CH2:35][CH2:34][CH:33]([NH2:37])[CH2:32]1>>[F:17][C:15]1[C:14]([C:18]#[C:19][C:20]([OH:23])([CH3:22])[CH3:21])=[CH:13][C:12]2[C:6]3[N:7]([C:24]([C:25]([NH:37][CH:33]4[CH2:34][CH2:35][CH2:36][N:31]([CH3:30])[CH2:32]4)=[O:27])=[C:4]([C:1]([NH2:2])=[O:3])[N:5]=3)[CH2:8][CH2:9][O:10][C:11]=2[CH:16]=1

Participants

3

Reactant 2

HCID 177503421-Methylpiperidin-3-amine dihydrochlorideHCID 866931712-Carbamoyl-9-fluoro-10-(3-hydroxy-3-methyl-but-1-ynyl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-3-carboxylic acid

Product 1

HCID 86693179(+/-) 9-fluoro-10-(3-hydroxy-3-methyl-but-1-ynyl)-N3-(1-methyl-3-piperidyl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-2,3-dicarboxamide

Procedure

2-Carbamoyl-9-fluoro-10-(3-hydroxy-3-methyl-but-1-ynyl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-3-carboxylic acid (0.06 g) was reacted with 1-methylpiperidin-3-amine dihydrochloride similar to as described in Example 2 to afford 22.3 mg of (±) 9-fluoro-10-(3-hydroxy-3-methyl-but-1-ynyl)-N3-(1-methyl-3-piperidyl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-2,3-dicarboxamide following reverse phase hplc purification. MS (Q1) 470 (M)+. 1H NMR (400 MHz, DMSO) δ 11.28 (d, J=7.4 Hz, 1H), 8.59 (d, J=8.4 Hz, 1H), 8.34 (s, 1H), 7.83 (s, 1H), 7.01 (d, J=10.6 Hz, 1H), 5.48 (s, 1H), 5.08-4.88 (m, 2H), 4.63-4.46 (m, 2H), 3.99-3.83 (m, 1H), 2.74-2.64 (m, 1H), 2.48-2.42 (m, 1H), 2.06 (t, J=8.0 Hz, 1H), 1.97 (t, J=10.6 Hz, 1H), 1.75 (m, J=13.8 Hz, 2H), 1.59-1.51 (m, 1H), 1.49 (s, 6H), 1.36-1.19 (m, 1H).

Sources & evidence

ORD record
ord-4f8d9f19865d49a7878fa0fd4f987fdb
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

Loading…